Process for producing antihalation photographic article



Patented Nov. 14, 1950 I UNITED STATES PATENT OFFICE rnoo'nss FOR PRODUCING ANTIHALATION V 1 r v i PHOTOGRAPHIC ARTICLE i Andr Emile Van Dormael, Heverlee-Louvain, and N Laurent Aloys Van der Auwera, Mortsel-Ant- [\PR 183i werp, Belgium,- assignors to Gevaert Photo- Producten V., Mortsel-Antwerp, Belgium, 21. company of Belgium No Drawingr Application September 23, 1947, Se-

rial No. 775,741. In Great Britain September 1 Claim. (01. 117--34) This invention relates to colored photographic This reaction may be represented as renews: layers, especially tov anti-halationand filter HI layers and to themanufacture thereof.

It is already known to prepare hemitricarbox- CH3 onoles by the following reaction: 5 HC--QH =0 FORMULAI' a )Leimrt 1?: 0 =0 +"HQN A;=C'-CHi-l-'Ar-NEFCH CH JEEOHFCH N Ar xcan 1': a on AFC-0:0 H+-oH=on c =eH- Nn-iu nn-on=on -cn=o-cn=c-c=o P Q 0= HS wherein Y 02115 P=an organicgroup; The reaction runsmore easily in an acid me- Q=an organic group, dium. or P andv Q together=the= non-metallic. atoms The starting product according to the above ne ary f r ompletinga cy lic a i l eu i general formula (II) may be prepared with ease Ar=anary1 group, from furfurol and; a compound with reactive A=an atom of'th'e chalcogeng-roup'. methylene group:

Hemitricarboxonoles containing an hydroxyl 2 substitutent in the. polymethine chain, however, L

are not known hitherto.

It is an object of the present invention to, provicle a new process for the manufacture of 'photographic layers, especially anti-halationand filter layers.

Another object of the present invention isto provide new eoloredphotographic layers;

Still a further object oft-he present invention is to provide-photographicmaterial containing-a colored layer accordingtotmsvinvention; The following examples illustrate the inven- NOW we-havefoundthat Verywen coloredhphm tion more clearly, Without limiting, however; its tographic layers, especially anti-halationor filscopeaccording to the'kn'own methods.

It is possible to addkn'own anti-halation": or filter dyestuffs to the solutionused for coating on a new coloredphotographic layer. said soln tion may be incorporated in a colloid layer, or to said solution may be a'dded'acolloid binder, or it may be coated or. spread Without the assistance of a colloid binder;

ter layers, may beobtained-by coating aphoto- Example 1 graphic. support or layer with solutionofl an 10 g. furfurylidene-acetyl-acetic acid ethyl aromatic amine and a compound of the general ester FormulaII Iv II 40 HCCH H -CH=C-C=A =0 l I al OH=$ Q wherein O O O C2115 P=an organic group such as CN, COOH, carbprepared from furfurol and acetyl-acetic ethyl alkoxy,acyl, ester according to the particulars given by E. Q=an organic group such as acyl, aryl, alkyl- Knoevenagel in Ber. 31 (1898) 734, dissolved in amino, arylamino, hydroxyl, alkoxyl, carboxyl, cm. of ethyl alcohol, are treated with 7 g. carbalkoxy, anthranilic acid dissolved in 90 cm. ethyl alcoor P and Q together=the non-metallic atoms hol, and next with 14 g. methylene-disalicylic necessary for completing a heterocyclic nuacid in cm. ethyl alcohol. cleus, occasionally having a fused-on arylene After spreading this solution upon the rear group, surface of a photographic material, an intense A=an atom of the chalcogen group. violet anti-halation layer with good covering power and lacquer properties is obtained. The probable formula is:

C O OH CzH O Ha Example 2 13 g. furfurylidene-4-methyl-3-phenyl-l-pyrazolone-5 prepared from furfurol and methyl-3-phenyl-1- pyrazolone-5 according to the instructions given by J. Tambor in Ber. 33 (1900) 870, dissolved in 250 cm. of ethyl alcohol, are treated with 5 g. aniline in 20 cm. of ethyl alcohol and with 14 g. methylene-disalicylic acid in 140 cm. ethyl alcohol. After spreading this solution upon the rear surface of a photographic material, an intense blue anti-halation layer with good covering power and lacquer properties is obtained.

The probable formula is:

VII

Example 3 6,5 g. furfurylidene-l-methyl-3-phenyl-l-pyrazolone-5, dissolved in 150 cm. ethyl alcohol, are treated with 3 g. N-methyl-aniline in 20 cm. alcohol and '7 g. methylene-disalicylic acid in 90 cm. alcohol. After spreading this solution upon a glass plate, an anti-halation iayer with the same properties as in the foregoing example is obtained.

The probable formula is:

VIII

4 Example 4 2,4 g. furfurylidene-cyan-acetic acid anilide HO--CH ON H CH= dissolved in 100 cm. ethyl alcohol are treated with 4.2 g. piperidine in cm. ethyl alcohol and 2.5 g. methylene-disalicylic acid in cm. ethyl alcohol. After spreading this solution upon a glass plate, an intense red anti-halation layer with good covering power and lacquer properties is obtained.

Probable formula according to Formula X REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES PATENTS Number Name Date 1,631,421 Lohofer June 7, 1927 1,900,459 Moyse Mar. '7, 1933 1,939,171 Hickman Dec. 12, 1933 2,158,287 Konig May 16, 1939 2,186,624 Brooker Jan. 9, 1940 2,199,542 Konig May '7, 1940 2,258,609 Hill Oct. 14, 1941 2,322,006 Fierke et a1 June 15, 1943 

